Trifluoroacetic acid → 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

HRID 1062782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062782
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12](C(OC(C)(C)C)=O)=[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:10]([CH3:34])[N:9]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl.[Cl-].[NH4+]>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=2)(=[O:22])=[O:23])[N:10]([CH3:34])[N:9]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 22282018tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 222819172-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate (Preparation 9) (1.48 g) in dichloromethane (20 ml) was added trifluoroacetic acid (10 ml), at room temperature. The reaction mixture was stirred at room temperature for 2.5 hours and then refluxed for 3 hours. The reaction mixture was then diluted with a saturated solution of aqueous ammonium chloride (20 ml), and the aqueous was then extracted with ethyl acetate (2×20 ml). The organics were dried with magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by chromatography on a suction column packed with silica eluted with ethyl acetate:hexane (3:5) to yield the desired product as an off white solid (200 mg).

Aufarbeitung

  1. customat room temperature
  2. temperaturerefluxed for 3 hours
  3. extractionthe aqueous was then extracted with ethyl acetate (2×20 ml)
  4. dry with materialThe organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by chromatography on a suction column
  8. washeluted with ethyl acetate:hexane (3:5)

Quellen und Nachweise

ORD-Eintrag
ord-d89db2f68b8241ae83a305faff8da471
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

Notizen zur Reaktion

Wird geladen…